Radical Cations of Bridged Bicyclo[5.1.0]octa-2,5-dienes—Open-Shell Bis-Homoaromatic Systems

Heinz D. Roth, Christopher J. Abelt

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

The radical cations of a series of bridged bicyclo[5.1.0]octa-2,5-dienes have been generated by photoinduced electron transfer to strong electron acceptors (chloranil, fluoranil) in solution. Chemically induced dynamic nuclear polarization effects observed during the reactions of simple bridged systems (1b-d,j) indicate that the intermediates are bis-homoaromatic (BHA) systems of B2 symmetry. These are the first homoaromatic radical cations of any structure type. Introduction of substituted exo-methylene groups as bridging units (1e-i) leads to a composite structure type with contributions from bis-homoaromatic structures of A2 and B2 symmetry and/or from a vinylcyclopropane structure (VCP) with an antisymmetric singly occupied molecular orbital.

Original languageEnglish (US)
Pages (from-to)2013-2019
Number of pages7
JournalJournal of the American Chemical Society
Volume108
Issue number8
DOIs
StatePublished - Jan 1 1986
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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